2-Methylbenzylamine → HCID 59564751, compound

HRID 383724Notes

Reaction equation

HRID 383724 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][NH:11][C:12]=2[CH:13]([CH3:15])[CH3:14])[CH:5]=[CH:4][N:3]=1.[CH3:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20]>CS(C)=O.CCOC(C)=O>[CH:13]([C:12]1[NH:11][N:10]=[CH:9][C:8]=1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:20][CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[CH3:16])[CH:7]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 69932-MethylbenzylamineHCID 67417340HCID 67417340, compound

Product 1

HCID 59564751HCID 59564751, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-fluoro-4-(5-isopropyl-1H-pyrazol-4-yl)-pyridine (30 mg, 0.15 mmol) in anhydrous DMSO (0.25 mL) is added 2-methyl-benzylamine (37 uL, 0.3 mmol). The reaction mixture is stirred at 150° C. overnight, diluted with EtOAc, and washed with water and brine. The organic layer is dried over sodium sulfate and concentrated in vacuo. The crude product is purified by preparative HPLC to provide 18.8 mg of [4-(5-isopropyl-1H-pyrazol-4-yl)-pyridin-2-yl]-(2-methyl-benzyl)-amine. (Example 1)

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-c7ea052c6d594a52a0c9531dda5f3da7
Source dataset
uspto-grants-2013_02
Patent number
US08367687B2

Reaction notes

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